Convenient approach to ω-aminoalkylthiophenes. Issue 17 (27th April 2016)

• Record Type: Journal Article
• Authors: Shvydenko, Tetiana; Nazarenko, Kostiantyn; Shvydenko, Kostiantyn; Filimonchuk, Serhii; Vlasenko, Yurii; Tolmachev, Andrei; Kostyuk, Aleksandr
• Is Part Of: Tetrahedron letters. Volume 57:Issue 17(2016)
• Page Start: 1909
• Page End: 1911
• Publication Date: 2016-04-27
• Subjects: α-Halo ketones -- Thieno[2, 3-c]azepine -- Thieno[2, 3-c]azocine -- Reduction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.03.066
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Five- through seven-membered cyclic enaminoesters. A facile method for the synthesis of ω-aminoalkylthiophenes. Intramolecular cyclization of ω-aminoalkylthiophenes. Thieno[2, 3- c ]azepine and thieno[2, 3- c ]azocine derivatives. Abstract: Starting from readily accessible cyclic enaminoesters, arylisothiocyanates and α-haloketones, a facile method for the synthesis of ω-aminoalkylthiophene hydrobromides was developed. It was shown that in the first step cyclic enaminoesters react with arylisothiocyanates exclusively at the enamine position. Upon treatment with base, free 5-aminopentylthiophenes were prepared. In the case of shorter alkyl substituents (4-aminobutyl and 3-aminopropyl) the free ω-aminoalkylthiophenes undergo intramolecular condensation of the amino and ketone groups affording novel fused heterocycles—thieno[2, 3- c ]azepine and thieno[2, 3- c ]azocine.